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Abstract

Major developments in the chemistry of carbazoles until 1960 arose mainly as a result of their use in the dye stuff and polymer industries although carbazole itself (1) was discovered in coal tar in 1872 by Graebe and Glazer (53). Since the report of the first carbazole alkaloid murrayanine (2) from Murraya koeinigii Spreng and the antibiotic properties of these alkaloids in 1965 by Chakraborty et al. (22, 31), there has been wider interest on the structure, synthesis and biochemical properties of these compounds. At present more than one hundred alkaloids are known and various biochemical and medicinal properties of this group of compounds have been investigated. Several reviews relating to carbazole alkaloids have appeared since 1971 (67,18, 19, 20, 56, 11). The present review relates to work reported after the previous review (11) and earlier results not included therein.

Keywords

Methoxy Group Tetrahedron Letter Ultraviolet Absorption Spectrum Electrophilic Aromatic Substitution Carbazole Derivative 
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References

  1. 1.
    Akugin, E., and U. Pindur: Chemische Eigenschaften und Synthese-Verfahren von 3-Vinylindolen. J. Heterocyclic Chem. 22, 585 (1985).Google Scholar
  2. 2.
    Albrecht, W.L., and R.W. Fleming: Bis-basic Esters and Amides of Carbazoles. US. 3932456 (C.A. 84, 150499t, 1976 ).Google Scholar
  3. 3.
    Al-Ekabi, H., and P. De Mayo: The Cds Photo-induced Dimerisation of N-Vinyl Carbazoles. Tetrahedron 42, 6277 (1986).Google Scholar
  4. 4.
    Ascalone, V., and L. Dalbo: Rapid and Simple Detection of Carpofen in Plasma by HPLC with Fluorescence Detection. J. Chromatography 276, 230 (1983).Google Scholar
  5. 5.
    Banderanayake, M., M.J. Begeley, B.O. Brown, D.G. Clarke, L. Crombie, and D.A. Whiting: Synthesis of Acridone and Carbazole Alkaloids Involving Pyridine Catalysed Chromene Formation: Crystal and Molecular Structure of Dibromocannabicyclol and Its Bearing on the Structures of Cyclol Alkaloids. J. Chem. Soc. Perkin I, 999 (1974).Google Scholar
  6. 6.
    Beecham Group: Antiemetics. J.P. 61 21252/1986 (C.A. 106, 78, 761 g, 1987 ).Google Scholar
  7. 7.
    Bergman, J., and B. Pelcman: Synthesis of Carbazoles Related to Carbazomycin, Hyellazole and Ellipticine. Tetrahedron 44, 5215 (1988).Google Scholar
  8. 8.
    Bergman, J., and R. Carlson: A Novel Synthesis of 2-Amino and 2-Hydroxycarbazoles. Tetrahedron Letters 4051 (1978).Google Scholar
  9. 9.
    Bhattacharyya, L., S.K. Roy, and D.P. Chakraborty: Structure of the Carbazole Alkaloid Isomurrayazoline from Murraya koenigii Spreng. Phytochem. 21, 2432 (1982).Google Scholar
  10. 10.
    Bhattacharyya, L., S. Roy, S. Chatterjee, and D.P. Chakraborty: Murrayazolinol—A Minor Carbazole Alkaloid from Murraya koenigii Spreng. J. Indian Chem. Soc. 66, 140 (1989)Google Scholar
  11. 11.
    Bhattacharyya, P., and Chakraborty, D.P.: Carbazole Alkaloids. In: Fortschr. Chem. Organ. Naturstoffe, Vol. 52, pp 159. ( W. Herz, H. Grisebach, and G.W. Kirby, Eds.) Wien, N.Y.: Springer 1987.Google Scholar
  12. 12.
    Bhattacharyya, P., M. Sarkar, A.K. Biswas, and D.P. Chakraborty: Iodine Promoted Thermal Cyclisation of Anthranilic acid. J. Indian Chem. Soc. 46, 328 (1979).Google Scholar
  13. 13.
    Birch, A.J., A.J. Leipa, and G.R. Stephenson: Organometallic Compounds in Organic Synthesis: Some Tricarbonyl (Cyclohexadienyl) Iron Cations and Nitrogen Containing Nucleophiles. Tetrahedron Letters 3565 (1979).Google Scholar
  14. 14.
    Bisset, N.G., A.K. Choudhury, and M.D. Walker: Occurrence of N-Cyano Alkaloids in Asian Strychnos Species. Phytochem. 13, 255 (1974).Google Scholar
  15. 14a.
    Canas-Rodriquez, A., and A. Mateo-Barnardo: Tetrahydrocarbazoles: Part-II. Tricyclic Inhibitors of Gastric acid Secretion. An. Quim. Ser. C. 81 254 (1985).Google Scholar
  16. 15.
    Chakrabarti, A., and D.P. Chakraborty: Photochemical Rearrangement of Pyranocarbazole Alkaloids: Part 1. Tetrahedron Letters 29, 6625 (1988).Google Scholar
  17. 16.
    Chakrabarti, A., and D.P. Chakraborty: Novel Access to Bis-Carbazoles Alkaloids: Substituent Effect on the Efficiency and Regioselectivity in BF3–Et20 Mediated Intermolecular coupling of Pyranocarbazole Alkaloids. Tetrahedron 45 7007 (1989).Google Scholar
  18. 17.
    Chakrabarti, A., G.K. Biswas, and D.P. Chakraborty: Photo-Fries Rearrangement in N-Sulphonyl Carbazoles. Tetrahedron 45, 5059 (1989).Google Scholar
  19. 18.
    Chakraborty, D.P.: Carbazole Alkaloids. In: Fortschr. Chem. Organ. Naturstoffe, Vol. 34, pp. 299 (W. Herz, H. Grisebach, and G.W. Kirby, Eds.) Wien-New York, Springer: 1977.Google Scholar
  20. 19.
    Chakraborty, D.P.: Some Aspects of Carbazole Alkaloids. Planta Medica 39, 97 (1980).Google Scholar
  21. 20.
    Chakraborty, D.P.: Twenty Years of Carbazole Alkaloids. Trans. Bose. Res. Inst. 47 49 (1984).Google Scholar
  22. 21.
    Chakraborty, D.P.: Some Newer Aspects of Plant Alkaloids. J. Indian Chem. Soc. 66 843 (1989).Google Scholar
  23. 22.
    Chakraborty, D.P., B.K. Barman, and P.K. Bose: On the Constitution of Murrayanine, a Carbazole Derivative Isolated from Murraya koenigii Spreng. Tetrahedron 21 681 (1965).Google Scholar
  24. 23.
    Chakraborty, D.P., S. Roy, and A.K. Dutta: Thermal Synthesis of Nor-girinimbine and Its Linear Isomer: A New Synthesis of Girinimbine. J. Indian Chem. Soc. 64 215 (1987).Google Scholar
  25. 24.
    Chowdhury, B.K., A. Mustafa, M. Garba, and P. Bhattacharyya: Carbazole and 3-Methylcarbazole from Glycosmis pentaphylla. Phytochem. 26 2138 (1988).Google Scholar
  26. 25.
    Coats, I.H., J.A. Bell, D.C. Humber, and G.B. Ewan: Tetrahydrocarbazolone Derivatives, E.P.191562 (CA. 105 226579u, 1986).Google Scholar
  27. 26.
    Coats, I.H., J.A. Bell, D.C. Humber, and G.B. Ewan:Substituted (Imidazolylmethyl)carbazolones as 5-Hydroxytryptamine Antagonists, Their Preparations and Pharmaceutical Formulation. E.P. 210840 (C.A. 106 15675b, 1987).Google Scholar
  28. 27.
    Cone, M.C., P.J. Seaton, K.A. Halles, and S.J. Gould: New Products Related to Kinamycin from Streptomyces murrayamaensis: Taxonomy, Production, Isolation and Biological Properties. J. Antibiotics 42, 179 (1989).Google Scholar
  29. 28.
    Das, B.P.: Some Investigations of the Pesticidal Properties of Carbazoles. International Pest Control 31, 144 (1989).Google Scholar
  30. 29.
    Das, B.P., and B. Chowdhury: Search for Potential Larvicides from Carbazoles. Trans. Bose Inst. 47 91 (1984).Google Scholar
  31. 30.
    Das, B.: Ph.D. Thesis, Calcutta University 1982.Google Scholar
  32. 31.
    Das, K.C., D.P. Chakraborty, and P.K. Bose: Antifungal Activity of Some Constituents of Murraya koenigii Spreng. Experientia 21, 340 (1965).Google Scholar
  33. 32.
    Dean, F.M.: Natural Coumarins. In: Fortschr. Chem. Organ. Naturstoffe, Vol. 9, pp. 225 ( L. Zechmeister, Ed.) Wien: Springer. 1952.Google Scholar
  34. 33.
    Dewar, D., V. Glover, J. Elsworth, and M. Sandler: Equal and Other compounds from Bovine Urine as Monoamine Oxidase Inhibitors. J. Neural. Trans. 65, 147 (1986) (C.A. 105 72468t, 1986).Google Scholar
  35. 34.
    Dobson, R.L.M., A.P. Dsilva, S.J. Weeks, and V.A. Fassel: Multidimensional Laser-based Instrument for Characterisation of Environmental Samples for Poly-cyclic Aromatic Compounds. Anal. Chem. 58, 2129 (1986).Google Scholar
  36. 35.
    Domanski, A., and J.B. Kyz1ol: Synthesis of Bis-Basic Substituted 9-ethylcarbazoles. Pol. J. Chem. 59, 613 (1985).Google Scholar
  37. 36.
    El-Gazzar, M.A., A.M. El-Naggar, F.S.M. Ahmed, and A.M. Abdelsalem: Synthesis and Biological Activity of Some New Substituted Aminoacyl Carbazole Derivatives. Arab. Galf. J. Sci. Res. 1, 131 (1983) (C.A. 100, 19 2230c, 1984 ).Google Scholar
  38. 37.
    Ferris, R.M.: Treatment of Drug Induced Psychosis. U.S. US 4588728 (C.A. 105, 54624m, 1986 ).Google Scholar
  39. 38.
    Ferris, R.M., F.L.M. Tang, K.J. Chang, and A. Russel: Evidence that the Potential Antipsychotic Agent Rincazole (BW234 U) is Specific Competitive Antagonist of Sigma Sites in Brain. Life Science 38, 2329 (1986).Google Scholar
  40. 39.
    Ferris, R.M., H.L. White, F.L.M. Tang, A. Russel, and M. Harfenist: Rincazole (BW234 U) Novel Antipsychotic Agent Whose Mechanism of Action Cannot be Explained by a Direct Blockade of Postsynaptic Dopaminergic Receptors in Brain. Drug. Der. Res. 9, 171 (1987) (C.A. 106, 27732j, 1987 ).Google Scholar
  41. 40.
    Filimonov, V.D., T.A. Filippova, V.P. Lopatinskii, M.M. Sukhoroslova, and N.V. Stepanov: Carbon 13-NMR of N-substituted carbazoles. Transfer of Electronic Effects of Substituents Through Nitrogen to Carbazole Ring. Khim. Geterotsiki Soedin 9, 1184 (1988) (C.A. 106, 195772r, 1987 ).Google Scholar
  42. 41.
    Furukawa, H., C. Ito, M. Yogo, and T.S. Wu: Structures of Murrayastine, Murrayaline and Pyrayafoline: Three New Carbazole Alkaloids from Murraya euchrestifolia. Chem. Pharm. Bull. 33, 1320 (1985).Google Scholar
  43. 42.
    Furukawa, H., M. Yogo, C. Ito, T.S. Wu, and C. Kuoh: New Carbazoloquinones Having Dimethyl Pyran Ring System. Chem. Pharm. Bull. 33, 1320 (1985).Google Scholar
  44. 43.
    Furukawa, H., T.S. Wu, and C. Kuoh: Dihydroxygirinimbine, a new Carbazole Alkaloid from Murraya euchrestifolia. Heterocycles 23, 1391 (1985).Google Scholar
  45. 44.
    Furukawa, H., T.S. Wu, and C. Kuoh: Structures of Murrafoline -B and -C, New Binary Carbazole Alkaloids from Murraya euchrestifolia. Chem. Pharm. Bull. 33, 12611 (1985).Google Scholar
  46. 45.
    Furukawa, H., T.S. Wu, and T. Ohta: Bismurrayafoline-A and -B, Two Novel “Dimeric” Carbazole Alkaloids from Murraya euchrestifolia. Chem. Pharm. Bull. 31, 4202 (1983).Google Scholar
  47. 46.
    Furukawa, H., T.S. Wu, T. Ohta, and S. Kuoh: Chemical Constituents of Murraya euchrestifolia Hayata, Structures of Novel Carbazolquinones and Other Carbazole Alkaloids. Chem. Pharm. Bull. 33, 4132 (1985).Google Scholar
  48. 47.
    Furusaki, A., M. Matsui, T. Watanabe, S. Omura, A. Nakagawa, and T. Hata: The Crystal and Molecular Structure of Kinamycin C p-Bromobenzoate. Israel J. Chem. 10, 173 (1972).Google Scholar
  49. 48.
    Gallagher, T., and P. Magnus: New Methods for Alkaloid Synthesis. Generation of Indole-2,3-Diquinomethanes as a Route to Indole Alkaloids. Tetrahedron 37, 3889 (1981).Google Scholar
  50. 49.
    Ghosh, S., T.K. Das, D.B. Datta, and S. Mehta: Studies on Enamides Part-1: Photochemical Rearrangement of N-Aroyl Carbazoles. Tetrahedron Letters 28, 4611 (1987).Google Scholar
  51. 50.
    Glaxo Group: Preparation of Tetrahydrocarbazole Derivatives as Serotonin Antagonists. Jr. Eur. Pat. Appl., E.P. 219, 193/1986 (C.A. 107 176032d, 1987) and previous references.Google Scholar
  52. 51.
    Griffith, W.P., S.V. Ley, G.P. Whitocomb, and A.D. White: Preparation and Use of tetra n-butylammonium Perruthenate (TBAP reagent) and Tetra-n-Propylammonium Perruthenate (TPAP reagent) as New Catalytic Oxidants for Alcohols. J.C.S. Chem. Commun. 1625 (1987).Google Scholar
  53. 52.
    Grellmann, K.H., and U. Schmitt: Reactivity and Decay Pathways of Photo-excited Anilino-naphthalene. J. Amer. Chem. Soc. 104, 6267 (1982).Google Scholar
  54. 53.
    Graebe, C., and C. Glazer: Ueber Carbazol. Chem. Ber. 5, 12 (1872).Google Scholar
  55. 54.
    Hata, T., S. Omura, Y. Iwai, A. Nakagawa, M. Otani, S. Ito, and T. Matsuya: A New Antibiotic Kinamycin. Fermentation, Isolation, Purification and Properties. J. Antibiotics 24, 353 (1971).Google Scholar
  56. 55.
    Hausberg, H.H., and H. Bettcher: Tetrahydrocarbazole Derivatives. Ger. Pat. DE 3,30094 (C.A. 101, 210979f, 1984 ).Google Scholar
  57. 56.
    Husson, H.: Simple Indole Alkaloids Including 13-Carbolines and Carbazoles In: Alkaloids, Vol. 26, pp. 1 ( Arnold Brossi Ed.) New York: Academic Press. 1985.Google Scholar
  58. 57.
    Ignatiadis, I., M. Kuroki, and P.J. Appino: Identification of Carbazole Derivatives in a Hydro Treated Gas Oil by Gas Chromatography and Gas Chromatography-Mass Spectrophotometry. J. Chromatography 366, 251 (1986).Google Scholar
  59. 58.
    Ito, C., T. Wu, and H. Furukawa: Three New Carbazole Alkaloids from Murraya euchrestifolia. Chem. Pharm. Bull. 35, 450 (1987).Google Scholar
  60. 59.
    Ito, C., T. Wu, and H. Furukawa: New Carbazole Alkaloids from Murraya euchrestifolia. Chem. Pharm. Bull. 36, 2377 (1988).Google Scholar
  61. 60.
    Ito, C., T. Wu, and H. Furukawa: The Structures of Some New Carbazole Alkaloids. IUPAC Symp. New Delhi, Feb. 4–7, 1990, p. 259.Google Scholar
  62. 61.
    Ito, S., T. Matsuya, S. Omura, M. Otani, A. Nakagawa, Y. Iwai, M. Ohtani, and T. Hata: A New Antibiotic, Kinamycin. J. Antibiotics 23, 315 (1970).Google Scholar
  63. 62.
    Jackson, G.D.F., and W.H.F. Sasse: Synthetical Applications of Activated Metal Catalysts. XXI. The Formation of Carbazole from Aniline and Related Compounds in Presence of Degassed Raney Nickel. Austr. J. Chem. 17, 347 (1964).Google Scholar
  64. 63.
    Joule, J.: Recent Advances in 9H Carbazoles. In: Advances in Heterocyclic Chemistry, Vol. 35, pp. 83. ( A. Katritzky Ed.) New York: Academic Press 1984.Google Scholar
  65. 64.
    Kamaruzzaman, S. Roy, and D.P. Chakraborty: Mumpamine from Glycosmis pentaphylla. Phytochem. 28, 677 (1989).Google Scholar
  66. 65.
    Kane, V., A.R. Martin, and P.A. Peters: The Non-regiospecific Condensation of Citral and 2-Hydroxycarbazole. Heterocycles 16, 1445 (1981).Google Scholar
  67. 66.
    Kaneda, M., T. Naid, T. Kitahara, and S. Nakamura: Carbazomycin G and H, Novel Carbazomycin Congeners Containing a Quinol Moiety. J. Antibiotics 41, 602 (1988).Google Scholar
  68. 67.
    Kapil, R.S.: Carbazole Alkaloids. In: Alkaloids, Vol. 13, pp. 273. ( R.H.F. Manske, Ed.) New York, London, Academic Press. 1971.Google Scholar
  69. 68.
    Karmakar, T., M. Mukherjee, and D.P. Chakraborty: Some Urea Derivatives as Growth Inhibitors. Curr. Sci. 55, 828 (1986).Google Scholar
  70. 69.
    Katritzky, A.R., G.W. Rewcastle, and L.M.V. De Miguel. Improved Syntheses of Substituted Carbazoles and Benzocarbazoles via Lithiation of the (Dialkylamino) methyl (Aminal) Derivatives. J. Org. Chem. 53, 794 (1988).Google Scholar
  71. 70.
    Kawasaki, T., Y. Nonaka, and M. Sakamoto: A New Efficient Synthesis of the 3Methoxy Carbazole Alkaloid Hyellazole. J. Chem. Soc. Chem. Commun. 43 (1989).Google Scholar
  72. 71.
    Kedderis, G.L., D.E. Douglas, R.N. Pandey, and P.F. Hollenberg: Oxygen-l8Studies of Peroxidase Catalysed N-Methyl Carbazole. Mechanism of Carbinolamine and Carboxyaldehyde Formation. J. Biol. Chem. 261, 15910 (1986).Google Scholar
  73. 72.
    Khazipov, R. Kh., R. Kh. Almaev, T.V. Korobova, and F.D. Davlyatov: Prevention of Growth of Bacteria. USSR Su 1212972 (C.A. 105 149668 t, 1986 ).Google Scholar
  74. 73.
    Knölker, H., and M. Bauermeister: The Total Synthesis of Carbazole Antibiotic Carbazomycin B and an Improved Route to Carbazomycin A. J. Chem. Soc. Chem. Commun. 1468 (1989).Google Scholar
  75. 74.
    Kondo, S., M. Katayama, and S. Marumo: Carbazomycinal and 6-Methoxycarbazomycinal as Aerial Mycellium Formation Inhibitory Substances of Streptoverticillium species. J. Antibiotics 39, 727 (1986).Google Scholar
  76. 75.
    Lontsi, D., J.F. Ayafor, B.L. Sondengam, J.D. Conolly, and D.S. Rycroft: The Use of Two Dimensional Proton Coupled 13C-NMR Spectrum in the Structural Elucidation of Ekebergenine, a New Carbazole Alkaloid from Ekebergia senegenalensis (Meliaceae). Tetrahedron Letters 26 4249 (1985).Google Scholar
  77. 76.
    Luk, K., L. Stern, M. Weigel, R.A. O’Brien, and N. Spirt: Isolation and Identification of `Diazepam Like’ Compounds from Bovine Urine. J. Nat. Prod. 46, 852 (1983).Google Scholar
  78. 77.
    Lednicer, D., and L.A. Mitcher: In: The Organic Chemistry of Drug Synthesis, vol. 3, pp. 168. New York: John Wiley & Sons. 1984.Google Scholar
  79. 78.
    Ljunggren, Bo, and K. Lundberg: In Vivo Phototoxicity of Nonsteroidal Antiinflammatory Drugs Evaluated by the Mousetail Technique: Photodermatology 2 377 (1985) (C.A. 104 81699 a, 1986).Google Scholar
  80. 79.
    Martin, T., and C.J. Moody: A New Route to 1-oxygenated Carbazoles. Synthesis of Murrayafoline-A. Tetrahedron Letters 26, 5841 (1985).Google Scholar
  81. 80.
    Masaki, M.T., S. Yushiro, S. Tsutomu, and N. Keiju: Pharmacological Studies on Carpofen, a New Non-steroidal Anti-inflammatory Drug in Animals. Nippon Kagaku Zasshi 73, 757 (1977) (C.A. 88, 69038c, 1978 ).Google Scholar
  82. 81.
    Mcphail, A.T., T.S. Wu, T. Ohta, and H. Furukawa: Structure of (±) Murrafoline, a Novel Biscarbazole Alkaloid from Murraya euchrestifolia. Tetrahedron Letters 24, 5377 (1983).Google Scholar
  83. 82.
    Mitra, A.R.: Ph.D. Thesis, Calcutta University, 1974.Google Scholar
  84. 83.
    Mobilio, D., C.A. Demeerson, and L.G. Humber: Substituted 2,3,4,9-Tetrahydro1-H-Carbazole-1-acetic acid and Its Use. US US4584312 (C.A. 105 133743c, 1986) and previous ref.Google Scholar
  85. 84.
    Moody, C.J., and P. Shah: Diels-Alder Reactivity of Pyrano [3,4-b] Indol-3-ones Part 4, Synthesis of Alkaloids Carbazomycin A, B, and Hyellazole. J.C.S. Parkin Trans 1, 2463 (1989).Google Scholar
  86. 85.
    Ngadjui, B.T., J.F. Ayafor, B.L. Sondengam, and J.D. Connolly: Quinolone and Carbazole Alkaloids from Clausena anisata. Phytochem. 28 1517 (1989).Google Scholar
  87. 86.
    Naid, T., T. Kitahara, M. Kaneda, and S. Nakamura: Carbazomycins C, D, E, F and G. Minor Components of Carbazomycins. J. Antibiotics 40, 157 (1987).Google Scholar
  88. 87.
    Narashimhan, N.S., and S.L. Kelkar: Alkaloids of Murraya koenigii Part III. Structure of Currayanine and Currayangine. Ind. J. Chem. 14B, 430 (1976).Google Scholar
  89. 88.
    Omura, S., A. Nakagawa, H. Yamada, T. Hata, A. Furusaki, and T. Watanabe: Structure of Kinamycin C and the Structural Relations Among Kinamycins A, B, C, D. Chem. Pharm. Bull. 19, 2428 (1971).Google Scholar
  90. 89.
    Omura, S., A. Nakagawa, H. Yamada, T. Hata, A. Furusaki, and T. Watanabe: Structures and Biological Properties of Kinamycin A, B, C, D. Chem. Pharm. Bull. 21, 931 (1973).Google Scholar
  91. 90.
    Padwa, A., and J.A. Lee: Photochemical Transformations of 2,2-Disubstituted Chromenes: J.C.S. Chem. Commun. 795 (1972).Google Scholar
  92. 91.
    Patel, B.P.J.: Citral Condensation: Towards Total Synthesis of Mahanimbine Isomers. Ind. J. Chem. 21B, 612 (1982).Google Scholar
  93. 92.
    Patel, B.P.J.: Cleaner Citral Condensation—Synthesis of Pyrano[2,3-a] Carbazoles. Synthetic Commun. 11, 823 (1981).Google Scholar
  94. 93.
    Patel, B.P.J.: Synthesis of Girinimbine Isomers—Pyrano [2,3-a] Carbazole Derivatives. Ind. J. Chem. 21B 20 (1982).Google Scholar
  95. 94.
    Patterson, A.M., and L.T. Capell: The Ring Index, p. 229, No 1675. New York: Reinhold. 1940.Google Scholar
  96. 95.
    Pecca, J.C., and S.M. Albonico: Trypnocides. I. Substituted 1,2,3,4-Tetrahydrocarbazoles. J. Med. Chem. 13, 327 (1970).Google Scholar
  97. 96.
    Pharr, D.Y., P.C. Uden, and S. Siggia: 3-(p-acetylphenoxy) Propyl Silane Bonded Phase for Liquid Chromatography of Basic Amines and Other Nitrogen Compounds. J. Chromat. Sci. 23, 391 (1985).Google Scholar
  98. 97.
    Pfeuffer, L., and U. Pindur: Diels-Alder-Reaktionen von 2’-substituierten-3vinyl-l-H-indolen zu neuen anellierten Indol-und Carbazole-Derivaten. Heiv. Chim. Acta 70, 1419 (1987).Google Scholar
  99. 98.
    Pindur, U.: New Diels-Alder Reactions with Vinylindoles: A Regio-and Stereo-controlled Access to Annelated Indoles and Derivatives. Heterocycles 27, 1253 (1988).Google Scholar
  100. 99.
    Pindur, U., and H. Erfanian-Ardoust: Indole 2,3 quinodimethanes and stable cyclic Analogues for Regio-and Stereocontrolled Syntheses of [b]-Annelated In-doles. Chem. Rev. 89, 1681 (1989).Google Scholar
  101. 100.
    Pindur, U., and L. Pfeuffer: [4+2]-Cyclo-addition to 4-Demethoxycarbazomycin. Heterocycles 26, 325 (1987).Google Scholar
  102. 101.
    Pindur, U., and L. Pfeuffer: New Structural Aspects of 3-Vinyl-IH-Indoles for Predicting the Outcome of Diels-Alder Reactions. Monatsh. Chem. 120, 27 (1989).Google Scholar
  103. 102.
    Pointek, J.A., and R.Y. Wang: Acute and Subchronic Effects of Rincazole (B234U) a Potential Antipsychotic Drug on A9 and A10 Dopamine Neurons in the Rat. Life Sci. 39, 651 (1986).Google Scholar
  104. 103.
    Raisz, L.G., C. Alander, C. Onklinkokx, and G.A. Rodan: Effects of Thiophen2-Carboxylic Acid and Related Compounds on Bone Resorption in Organ Culture. Calcif. Tissue Int. 37, 556 (1985) (C.A. 103, 206184s, 1985 ).Google Scholar
  105. 104.
    Rice, L.M., and K.R. Scot: 3-Substituted 1,2,3,4-Tetrahydrocarbazoles. J. Med. Chem. 13, 308 (1970).Google Scholar
  106. 105.
    Roy, S., A. Chakrabarti, and D.P. Chakraborty: Lewis Acid Catalysed Aliphatic Diazo-coupling. An Access to Nitrogen Heterocycles. Proc. Convention of Chemists (Ind. Chem. Soc.) C 34 (1986).Google Scholar
  107. 106.
    Roy, S., R. Guha, S. Ghosh, and D.P. Chakraborty: Biomimetic Hydroxylation Studies on Carbazole Alkaloids. Ind. J. Chem. 21B, 617 (1982).Google Scholar
  108. 107.
    Sakano, K., and S. Nakamura: New Antibiotics Carbazomycins A and B II. Structural Elucidations. J. Antibiotics 33, 961 (1980).Google Scholar
  109. 108.
    Saulnier, M.G., and C.W. Gribble: 4-Phenyl sulphonyl-4-H-Furo [3,4-b] Indole, a Stable Analogue of Indole-2,3-quinodimethane. Tetrahedron Letters, 5435 (1983).Google Scholar
  110. 109.
    Searl, A.J., F.C. Gee, and R.L. Wilson: In Oxygen radical in Chem. & Biol. (Proc. 3rd Int. Conf. 1983). (W. Bros, S. Manfered and C. Tait, Eds.) Berlin: David de Gruyter. (C.A. 100, 203140b, 1984 ).Google Scholar
  111. 110.
    Seaton, P.J., and S.J. Gould: New Products Related to Kinamycin from Streptomyces murayamaensis. Structures of Pre-Kinamycin, Keto-Anhydrokinamycin, and Kinamycins E and F. J. Antibiotics 42 189 (1989).Google Scholar
  112. 111.
    Seaton, P.J., and S.J. Gould: Kinamycin Biosynthesis Derivation by Excision of an Acetate Unit from a Single-chain Decaketide Intermediate. J. Amer. Chem. Soc. 109 5282 (1987).Google Scholar
  113. 112.
    Seaton, P.J., and S.J. Gould: Origin of Cyanamide Carbon of Kinamycin Antibiotics. J. Amer. Chem. Soc. 110 5912 (1988).Google Scholar
  114. 113.
    Sengupta, S.N.: Ph.D. Thesis, Calcutta University, 1979.Google Scholar
  115. 114.
    Sexton, W.A.: In: Chemical Constitution and Biological Activity, 3rd Edn., p. 306. London: F.N. Spon Ltd. 1973.Google Scholar
  116. 115.
    Shizuki, H., M. Kato, T. Ochiai, K. Matsui, and T. Morita: The Photochemical Rearrangements of N-Acetyl Diphenylamine and N-Acetyl Carbazole. Bull Chem. Soc., Japan 43, 67 (1970).Google Scholar
  117. 116.
    Sharma, K.S., and Sarita, CMR Spectral Studies of Substituted Carbazoles. Ind. J. Chem. 27B, 402 (1988).Google Scholar
  118. 117.
    Storch, E., H. Kirchner, K. Hueller, M.G. Maritinotti, and D. Gemsa: Enhancement by Carpofen or Indomethacin of Interferon Induction by 10Carboxymethyl-9-acridanone in Murine Cell Culture. J. Ger. Virol. 67, 1211 (1986) (C.A. 105, 35311r, 1986 ).Google Scholar
  119. 118.
    Stothers, J.B.: Carbon-13 NMR Spectroscopy, pp. 266. New York: Academic Press. 1972.Google Scholar
  120. 119.
    Tepaske, M.R., J.B. Gloer, D.T. Wicklow, and P.F. Dowd: An Antiviral Carbazole Alkaloid from Sclerotia of Aspergillus tubingensis. J. Org. Chem. 54, 4743 (1989).Google Scholar
  121. 120.
    Tepaske, M.R., J.B. Gloer, D.T. Wicklow, and P.F. Dowd: The Structure of Tubingensin B: A Cytotoxic Carbazole Alkaloid from Sclerotia of Aspergillus tubingensis. Tetrahedron Letters 30, 5965 (1989).Google Scholar
  122. 121.
    Torsi, A., M.P. Loria, G. Specchia, and D. Cassassima: In vitro Studies of Anti-inflammatory Activity of Carpofen. Eur. J. Rheumatol. Inflammation 5, 488 (1982) (C.A. 98, 46621e, 1983 ).Google Scholar
  123. 122.
    Udenfriend, S., C.T. Cark, J. Axelrod, and B.B. Brodu: Ascorbic Acid in Aromatic Hydroxylation I, a Model System of Aromatic Hydroxylation. J. Biol. Chem. 208, 731 (1954).Google Scholar
  124. 123.
    Wood, P.L., and P.S. Mcquade and S. Paul: Cyclindole and Flucindole Novel Tetrahydrocarbazoleamine Neuroleptics. Prog. Neuro-Psychopharmacol. Biol. Psychiatry 8, 773 (1984) (C.A. 102, 125458 m, 1985 ).Google Scholar
  125. 124.
    Yamasaki, K., M. Kaneda, K. Watanabe, Y. Ueki, K. Ishamaru, S. Nakamura, R. Nomi, N. Yoshida, and T. Nakajima: New Antibiotics Carbazomycin A and B. III. J. Antibiotics 36, 552 (1983).Google Scholar

Copyright information

© Springer-Verlag/Wien 1991

Authors and Affiliations

  • D. P. Chakraborty
    • 1
  • Shyamali Roy
    • 1
  1. 1.Comparative Phytochemical LaboratoryBose InstituteCalcuttaIndia

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